If Matt wins, I will pay him every last satoshi of my bet. To not do this would go against my word and honor.
Additionally, he is providing a great service by allowing people to hedge their situation.
This^
If you're into Pirate for any amount, your best bet (heh) is to wager up to 50% of that with Matt. The inverse, however, is not true. Buying Pirate debt
after making a wager with Matt is betting against yourself. Never do that. You always lose.
Logical fallacy.
If keeping Pirate debt debt and hedging it is a "best bet" then buying Pirate debt bet and hedging is equally the "best bet".
Conversely if buying Pirate debt and hedging it is a "bad bet" then someone with a with an existing debt shouldn't keep it they should sell it and thus keeping the Pirate debt and hedging it is equally bad.
If someone can buy then someone else can sell. One can't be bad and the other the "best bet".
Does your brain not comprehend logic. Is everything just luck and unicorns?
Of course, if you can sell it for 50% or better, that's probably a better deal. Taking a hedge bet like this reduces your risk from already purchased debt. Buying debt after making a bet like this only increases your risk.
Look at it this way:
Long ago, you invested in BS&T. At the time, you thought it was a good investment. Now it's looking like it's not, so you pick up some of Matt's action. If it was a bad investment, he'll pay you half (let's say) of what you lost. If it somehow turns out to be a good investment, still, you'll have to pay him half of that, so basically what you're doing is trading some of your Pirate risk for Matt risk, but they even out, so either way, you get half of what you've already risked. Even if he doesn't pay out, you're no worse off than you started, because before he did this, you would have lost 100% anyway.
The other way around, however, is not so beneficial. You start out with X Bitcoins. You bet some of that on Matt's venture. Half is easy to work with, so let's keep that. At this point, if Pirate defaults, and Matt doesn't pay, you still have X. If he does pay, you have 1.5X. If Pirate pays out, you have .5X, if you choose to pay out, otherwise you'll be labeled a scammer. If you then buy pirate debt, again, let's assume .5X worth, you now have X-Y Bitcoins (Y being the amount you paid for that debt). If Pirate doesn't pay out, and Matt does, you now have 1.5X-Y, less than you would have had if you had not bought the debt. If Pirate doesn't pay out, and Matt doesn't either, you still have X-Y, again, less than you would have had if you had not bought the debt. If Pirate does pay out (and for ease of math, we'll assume 100%, but that's by no means certain), you now have X-Y, less than you would have had if you had not made the bet at all, but more than if you had not bought the debt. (and, you'll note, less than you started with)
To sum up:
If you have already sunk money into Pirate, but aren't sure he'll pay back, it makes sense to hedge that money with a bet against Matt. Worst case scenario, you're no worse off, and best case scenario, you'll at least get some of what you've lost back.
If you have not yet sunk money into Pirate, but are pretty sure he won't pay back, it makes sense to bet against Matt.
If you have not yet sunk money into Pirate, but are pretty sure he
will pay back, it makes sense to buy Pirate debt.
Under no circumstances does it make sense to do both.